chromic acid in acetone 0.5 h; Ambient temperature;

1: 1.) AlCl3, 3.) NaHCO3 2: 1 N aq. HCl / CH2Cl2 3: 72 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / -78 °C 4: 55 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / Ambient temperature 5: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, RT 6: 72 percent / 10percent chromic acid / acetone / 0.5 h / Ambient temperature View Scheme

1: 72 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / -78 °C 2: 55 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / Ambient temperature 3: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, RT 4: 72 percent / 10percent chromic acid / acetone / 0.5 h / Ambient temperature View Scheme

1: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, RT 2: 72 percent / 10percent chromic acid / acetone / 0.5 h / Ambient temperature View Scheme

1: 55 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / Ambient temperature 2: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, RT 3: 72 percent / 10percent chromic acid / acetone / 0.5 h / Ambient temperature View Scheme